Recent developments in asymmetric catalysis in the presence of Chiral gold complexes

Synthesis

Volumn , Issue 10, 2011, Pages 1501-1514

  Pradal, Alexandre ^a   Toullec, Patrick Y ^a   Michelet, Véronique ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

alkenes; alkynes; allenes; asymmetric catalysis; cycloisomerization; domino processes; gold

Indexed keywords

ALKENES; ALKYNES; ALLENES; ASYMMETRIC CATALYSIS; CYCLOISOMERIZATIONS; DOMINO PROCESS;

ACETYLENE; CATALYSIS; GOLD; HYDROGENATION; ISOMERIZATION; NUCLEOPHILES; OLEFINS; OXYGEN;

GOLD COMPOUNDS;

(4,5) BIS (METHY)(2,2 DIMETHYL) 1,3 DIOXOLANE; 1 TERT BUTYL IMIDAZOLIDIN 2 ONE; ACRYLIC ACID DERIVATIVE; ACRYLONITRILE; ALDEHYDE; ALKENE; BORIC ACID; CARBON; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIETHYL 2 BENZYLIDENESUCCINIC ACID; DIETHYL 2 NAPHTHYLIDENESUCCINIC ACID; DIETHYLITACONATE; GOLD COMPLEX; METHYL ALPHA ISOCYANOCARBOXYLIC ACID; N BENZYL (1 PHENYLETHYLEIDENE)IMINE; NITROGEN; NUCLEOPHILE; OXAZOLINE DERIVATIVE; OXYGEN; PYRROLINE DERIVATIVE; SILVER; SILVER CHLORIDE; SODIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORIC ACID; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ASYMMETRIC CATALYSIS; CARBONYLATION; CHEMICAL BINDING; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; NUCLEOPHILICITY; REVIEW;

EID: 79955799172     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258465     Document Type: Review

References (107)

1. Trost B M., Acc. Chem. Res. 2002 35 695
2. Trost B M., Angew. Chem. 1995 107 285
3. Trost B M., Science 1991 254 1471
4. Anastas P T., Kirchhoff M M., Acc. Chem. Res. 2002 35 686
5. Anastas P T., Warner J C., Green Chemistry: Theory and Practice Oxford University Press Oxford 1998 11
6. For recent reviews on gold catalysis, see:, Hashmi A S. K., Angew. Chem. Int. Ed. 2010 49 5232
7. Hashmi A S. K., Bührle M, Aldrichimica Acta 2010 43 27
8. Shapiro N D., Toste F D., Synlett 2010 675
9. Das A, AbuSohel S M., Liu R.-S, Org. Biomol. Chem. 2010 8 860
10. AbuSohel S M., Liu R.-S, Chem. Soc. Rev. 2009 38 2269
11. Fürstner A, Chem. Soc. Rev. 2009 38 3208
12. Arcadi A, Chem. Rev. 2008 108 3266
13. Patil N T., Yamamoto Y, Chem. Rev. 2008 108 3395
14. Li Z, Brouwer C, He C, Chem. Rev. 2008 108 3239
15. Shen H C., Tetrahedron 2008 64 3885
16. Skouta R, Li C.-J, Tetrahedron 2008 64 4917
17. Hashmi A S. K., Rudolph M, Chem. Soc. Rev. 2008 37 1766
18. Muzart J, Tetrahedron 2008 64 5815
19. Gorin D J., Sherry B D., Toste F D., Chem. Rev. 2008 108 3351
20. Hashmi A S. K., Chem. Rev. 2007 107 3180
21. Fürstner A, Davies P W., Angew. Chem. Int. Ed. 2007 46 3410
22. Gorin D J., Toste F D., Nature 2007 446 395
23. Hashmi A S. K., Hutchings G J., Angew. Chem. Int. Ed. 2006 45 7896
24. Jimenez-Nunez E, Echavarren A M., Chem. Commun. 2007 333
25. Chianese A R., Lee S J., Gagné M R., Angew. Chem. Int. Ed. 2007 46 4042
26. Ma S, Yu S, Gu Z, Angew. Chem. Int. Ed. 2006 45 200
27. Hashmi A S. K., Angew. Chem. Int. Ed. 2005 44 6090
28. Höffmann-Röder A, Krause N, Org. Biomol. Chem. 2005 23 387
29. Haruta M, Gold Bull. 2004 37 27
30. Bond G. C, Thompson D. T, Catal. Rev. 1999 41 319
31. For recent reviews, see:, Bongers N, Krause N, Angew. Chem. Int. Ed. 2008 47 2178; and references cited therein
32. Widenhoefer R A., Chem. Eur. J. 2008 5382
33. Sengupta S, Shi X, ChemCatChem 2010 2 609
34. Ito Y, Sawamura M, Hayashi T, J. Am. Chem. Soc. 1986 108 6405
35. Togni A, Pastor S D., J. Org. Chem. 1990 55 1649
36. Sawamura M, Nakayama Y, Kato T, Ito Y, J. Org. Chem. 1995 60 1727
37. Melhado A D., Luparia M, Toste F D., J. Am. Chem. Soc. 2007 129 12638
38. Gonzales-Arellano C, Corma A, Iglesias M, Sanchez F, Chem. Commun. 2005 3451
39. Debono N, Iglesias M, Sanchez F, Adv. Synth. Catal. 2007 349 2470
40. Arnanz A, Gonzales-Arellano C, Juan A, Villaverde G, Corma A, Iglesias M, Sanchez F, Chem. Commun. 2010 46 3001
41. Corma A, Dominguez I, Doménech A, Fornés V, Gomez-Garcia C J., Rodenas T, Sabater M J., J. Catal. 2009 265 238
42. Zhang Z, Lee S D., Windehoefer R A., J. Am. Chem. Soc. 2009 131 5372
43. Bandini M, Eichholzer A, Angew. Chem. Int. Ed. 2004 43 2402
44. For reviews on metal-catalyzed allene activation, see:, Lopez F, Mascarenas J L., Chem. Eur. J. 2010 418
45. Hashmi A S. K., Angew. Chem. Int. Ed. 2000 39 3590
46. Zhang Z, Widenhoefer R A., Angew. Chem. Int. Ed. 2007 46 283
47. Lalonde R L., Sherry B D., Kang E J., Toste F D., J. Am. Chem. Soc. 2007 129 2452
48. Zhang Z, Bender C F., Widenhoefer R A., Org. Lett. 2007 9 2887
49. Lalonde R L., Wang Z J., Mba M, Lackner A D., Toste F D., Angew. Chem. Int. Ed. 2010 49 598
50. Liu C, Widenhoefer R A., Org. Lett. 2007 9 1935
51. Tarselli M A., Chianese A R., Lee S J., Gagné M R., Angew. Chem. Int. Ed. 2007 46 6670
52. Luzung M R., Mauleon P, Toste F D., J. Am. Chem. Soc. 2007 129 12402
53. Teller H, Flügge S, Goddard R, Fürstner A, Angew. Chem. Int. Ed. 2010 49 1949
54. Alonso I, Trillo B, Lüpez F, Montserrat F, Ujaque G, Castedo L, Lledüs A, Mascareüas J L., J. Am. Chem. Soc. 2009 131 13020
55. Gonzülez A Z., Toste F D., Org. Lett. 2010 12 200
56. Kleinbeck F, Toste F D., J. Am. Chem. Soc. 2009 131 9178
57. Hamilton G L., Kang E J., Mba M, Toste F D., Nature 2007 317 496
58. Aikawa K, Kojima M, Mikami K, Adv. Synth. Catal. 2010 352 3131
59. Aikawa K, Kojima M, Mikami K, Angew. Chem. Int. Ed. 2009 48 6073
60. Johansson M J., Gorin D J., Staben S T., Toste F D., J. Am. Chem. Soc. 2005 127 18002
61. Watson I D. G., Ritter S, Toste F D., J. Am. Chem. Soc. 2009 131 2056
62. Uemura M, Watson I D. G., Katsukawa M, Toste F D., J. Am. Chem. Soc. 2009 131 3464
63. Wilckens K, Uhlemann M, Czekelius C, Chem. Eur. J. 2009 15 13323
64. Hashmi A S. K., Hamzié M, Rominger F, Bats J W., Chem. Eur. J. 2009 15 13318
65. Murai M, Uenishi J, Uemura M, Org. Lett. 2010 12 4788
66. For recent reviews on cycloisomerization reactions of enynes, see:, Belmont P, Parker E, Eur. J. Org. Chem. 2009 35 6075
67. Le S I., Chatani N, Chem. Commun. 2009 371
68. Jiménez-Nüüez E, Echavarren A M., Chem. Rev. 2008 108 3326
69. Michelet V, Toullec P Y., Genüt J.-P, Angew. Chem. Int. Ed. 2008 47 7427
70. Zhang L, Sun J, Kozmin S, Adv. Synth. Catal. 2006 348 2271
71. Fairlamb I J. S., Angew. Chem. Int. Ed. 2004 43 1048
72. Lloyd-Jones G, Org. Biomol. Chem. 2003 1 215
73. Buisine O, Aubert C, Malacria M, Chem. Rev. 2002 102 813
74. Blum J, Beer-Kraft H, Badrieh Y, J. Org. Chem. 1995 60 5567
75. Fürstner A, Szillat H, Stelzer F, J. Am. Chem. Soc. 2000 122 6785
76. Fürstner A, Stelzer F, Szillat H, J. Am. Chem. Soc. 2001 123 11863
77. Nieto-Oberhuber C, Muüoz M P., Buüuel E, Nevado C, Cürdenas D J., Echavarren A M., Angew. Chem. Int. Ed. 2004 43 2402
78. Shibata T, Kobayashi Y, Maekawa S, Toshida N, Takagi K, Tetrahedron 2005 61 9018
79. Brissy D, Skander M, Jullien H, Retailleau P, Marinetti A, Org. Lett. 2009 11 2137
80. Nishimura T, Kawamoto T, Nagaosa M, Kumamoto H, Hayashi T, Angew. Chem. Int. Ed. 2010 49 1638
81. Chao C.-M, Beltrami D, Toullec P Y., Michelet V, Chem. Commun. 2009 6988
82. Martünez A, Garcüa-Garcüa P, Fernündez-Rodrüguez M A., Rodrüguez F, Sanz R, Angew. Chem. Int. Ed. 2010 49 4633
83. For selected examples on gold-catalyzed alkoxycyclization reactions of 1, n -enynes, see:, Méndez M, Muüoz M P., Echavarren A M., J. Am. Chem. Soc. 2000 122 11549
84. Méndez M, Muüoz M P., Nevado C, Cürdenas D J., Echavarren A M., J. Am. Chem. Soc. 2001 123 10511
85. Nevado C, Cürdenas D J., Echavarren A M., Chem. Eur. J. 2003 9 2627
86. Muüoz M P., Méndez M, Nevado C, Cürdenas D J., Echavarren A M., Synthesis 2003 2898
87. Nevado C, Charuault L, Michelet V, Nieto-Oberhuber C, Muüoz M P., Méndez M, Rager M.-N, Genüt J.-P, Echavarren A M., Eur. J. Org. Chem. 2003 706
88. Nieto-Oberhuber C, Muüoz M P., Buüuel E, Nevado C, Cürdenas D J., Echavarren A M., Angew. Chem. Int. Ed. 2005 44 6146
89. Zhang L, Kozmin S A., J. Am. Chem. Soc. 2005 127 6962
90. Mezailles N, Ricard L, Gagosz F, Org. Lett. 2005 7 4133
91. Sherry B D., Maus L, Laforzeta B N., Toste F D., J. Am. Chem. Soc. 2006 128 8132
92. Genin E, Leseurre L, Toullec P Y., Genüt J.-P, Michelet V, Synlett 2007 1780
93. Buzas A K., Istrate F M., Gagosz F, Angew. Chem. Int. Ed. 2007 46 1141
94. Chao C.-M, Toullec P Y., Michelet V, Tetrahedron Lett. 2009 50 3719
95. Li G, Liu Y, J. Org. Chem. 2010 75 2903
96. Muüoz M P., Adrio J, Carretero J C., Echavarren A M., Organometallics 2005 24 1293
97. Chao C.-M, Genin E, Toullec P Y., Genüt J.-P, Michelet V, J. Organomet. Chem. 2009 694 538
98. Matsumoto Y, Selim K B., Nakanishi H, Yamada K.-I, Yamamoto Y, Tomioka K, Tetrahedron Lett. 2010 51 404
99. Liu F, Yu Y, Zhang J, Angew. Chem. Int. Ed. 2009 48 5505
100. Liu F, Qian D, Li L, Zhao X, Zhang J, Angew. Chem. Int. Ed. 2010 49 6669
101. Sethofer S G., Meyer T, Toste F D., J. Am. Chem. Soc. 2010 132 8276
102. Toullec P Y., Blarre T, Michelet V, Org. Lett. 2009 11 2888
103. Fürstner A, Morency L, Angew. Chem. Int. Ed. 2008 47 5030
104. Leseurre L, Toullec P Y., Genüt J.-P, Michelet V, Org. Lett. 2007 9 4049
105. Böhringer S, Gagosz F, Adv. Synth. Catal. 2008 350 2617
106. Chao C.-M, Vitale M R., Toullec P Y., Genüt J.-P, Michelet V, Chem. Eur. J. 2009 15 1319
107. For the racemic version, see:, Toullec P Y., Genin E, Leseurre L, Genüt J.-P, Michelet V, Angew. Chem. Int. Ed. 2006 45 7427